EP0501735A1 - Antistatische Oberflächenmodifikation von Polymerisaten - Google Patents

Antistatische Oberflächenmodifikation von Polymerisaten Download PDF

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Publication number
EP0501735A1
EP0501735A1 EP92301546A EP92301546A EP0501735A1 EP 0501735 A1 EP0501735 A1 EP 0501735A1 EP 92301546 A EP92301546 A EP 92301546A EP 92301546 A EP92301546 A EP 92301546A EP 0501735 A1 EP0501735 A1 EP 0501735A1
Authority
EP
European Patent Office
Prior art keywords
antistatic agent
solvent
ammonium bromide
antistatic
solution
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP92301546A
Other languages
English (en)
French (fr)
Inventor
Dana Sorina Garcia
Joseph Silbermann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arkema Inc
Original Assignee
Elf Atochem North America Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Elf Atochem North America Inc filed Critical Elf Atochem North America Inc
Publication of EP0501735A1 publication Critical patent/EP0501735A1/de
Withdrawn legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04Coating
    • C08J7/06Coating with compositions not containing macromolecular substances
    • C08J7/065Low-molecular-weight organic substances, e.g. absorption of additives in the surface of the article
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04Coating
    • C08J7/044Forming conductive coatings; Forming coatings having anti-static properties
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2327/00Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
    • C08J2327/02Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/04Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
    • C08J2327/06Homopolymers or copolymers of vinyl chloride

Definitions

  • This invention is directed to imparting antistatic properties to a thermoplastic polymer, preferably a polyvinyl chloride polymer.
  • Antistatic agents have been applied to polymers by either an external or an internal method.
  • the external method which generally involves dipping or wiping a solution of antistatic agent on the polymer, has heretofore been inadequate.
  • the external process due to the nature of the solvent used, generally alcohol or water, does not result in an adequate incorporation of the antistatic agent into the polymer, and thus, results in almost complete loss of the antistatic property following washing.
  • the internal method which generally involves incorporation of an antistatic agent into the polymeric material prior to shaping into solid form, has also heretofore been inadequate.
  • the internal process has been largely uneconomical and inefficient because the antistatic agent is present substantially in the interior of the shaped article, where it does not function effectively to prevent surface static properties.
  • the internat process is also limited in the choice of antistatic agents and requires significantly large quantities of antistatic agent.
  • the problem addressed by the present invention is to provide new methods of conferring antistatic properties to thermoplastic polymers, materials for treating the polymers, and thermoplastic polymers obtainable thereby.
  • the invention relates to PVC polymers.
  • the present invention provides a permanence because the antistatic agent in the present invention exists not only on the surface of the PVC but also penetrates through the surface of the PVC.
  • the PVC may be contacted with the solution containing the antistatic agent in various ways.
  • the contacting may involve a dipping, spraying, wiping, coating, or other the process, provided that the PVC and the antistatic agent solution are contacted for a sufficient time to allow the antistatic agent to penetrate into the PVC.
  • the process disclosed in US-A-4770905 may be used.
  • the PVC and the antistatic agent solution are contacted for a sufficient time to allow the antistatic agent to penetrate into the PVC, the PVC can be washed with water and then subsequently dried.
  • R1 and R2 are selected such that they are soluble in the solvent and insoluble or only slightly soluble in water.
  • R1 and R2 can each be a substituted or non-substituted alkyl group of from 1-20 carbon atoms.
  • Examples of the (hexyl) n (octyl) m ammonium bromide antistatic agent are bihexyl bioctyl ammonium bromide, trihexyl octyl ammonium bromide, and tetrahexyl ammonium bromide.
  • Examples of the (heptyl) n (octyl) m ammonium bromide antistatic agent are biheptyl bioctyl ammonium bromide, triheptyl octyl ammonium bromide, and tetraheptyl ammonium bromide.
  • the ammonium halide antistatic agents are typically preferred over the 1-dodecylpyridinium antistatic agent because the ammonium halide antistatic agents are water insoluble but solvent soluble.
  • the 1-dodecylpyridinium antistatic agent is somewhat soluble in water and, hence, some of it may be removed from the PVC during washing. Nevertheless, the 1-dodecylpyridinium antistatic agent can be effectively used.
  • the solvent used for contacting the antistatic agent with the PVC can be any solvent which swells the PVC surface and which is soluble with the antistatic agent.
  • the solvent can be methylene chloride, dimethyl sulfoxide (DMSO) or N-methyl pyrrolidone (NMP).
  • the antistatic agent concentration by weight in the solvent is preferably from about 1% to about 30%, and more preferably from about 10% to about 20%.
  • the solution containing the antistatic agent is contacted with the PVC preferably from about 2 to about 60 seconds.
  • PVC samples (89 x 89mm) were dipped in a methylene chloride solution containing various concentrations of 1-dodecylpyridinium chloride monohydrate. Following the dipping process, the sample was washed with water and air dried.
  • the effect of the treatment was then evaluated by measuring the Surface Resistivity (Rs) and the Decay Time (sec).
  • the Surface Resistivity was measured according to ASTM D257 and the Decay Time according to the Fed. Test Method STD No. 1010, Method 4046. Untreated samples were also measured for comparative purposes.
  • the antistatic agent/CH2Cl2 embodying the invention also exhibited at least a 30 day degree of permanence as shown by the Rs values on day 1 and day 37 (see Table I).
  • PVC samples were dipped in a methylene chloride solution containing various concentrations of tetrahexyl ammonium bromide in the same manner as in Example 1.
  • Table 2 shows the results for the as treated samples.
  • Table 3 shows the degree of permanence after various post-treatments.
  • Table 4 shows the degree of permanence as a function of time.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
EP92301546A 1991-02-27 1992-02-25 Antistatische Oberflächenmodifikation von Polymerisaten Withdrawn EP0501735A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/662,206 US5169688A (en) 1991-02-27 1991-02-27 Antistatic surface modification of pvc
US662206 1991-02-27

Publications (1)

Publication Number Publication Date
EP0501735A1 true EP0501735A1 (de) 1992-09-02

Family

ID=24656805

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92301546A Withdrawn EP0501735A1 (de) 1991-02-27 1992-02-25 Antistatische Oberflächenmodifikation von Polymerisaten

Country Status (4)

Country Link
US (1) US5169688A (de)
EP (1) EP0501735A1 (de)
JP (1) JPH05214130A (de)
CA (1) CA2061605A1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994011421A1 (en) * 1992-11-06 1994-05-26 Pharmacia Biotech Ab A method of surface modification

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112521698A (zh) * 2020-12-09 2021-03-19 宁波保税区君一汽配科技有限公司 一种pvc塑料及其制备方法

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* Cited by examiner, † Cited by third party
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FR1293186A (fr) * 1960-04-14 1962-05-11 Ici Ltd Polymères organiques à propriétés antistatiques améliorées
GB921032A (en) * 1958-11-27 1963-03-13 Tokyo Shibaura Electric Co A method of manufacturing antistatic record discs
EP0134523A1 (de) * 1983-08-04 1985-03-20 General Electric Company Absorption von Additiven aus Lösungen in Polymeroberflächen
US4770905A (en) * 1986-12-23 1988-09-13 M&T Chemicals Inc. Process for surface modification of polymer articles

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Publication number Priority date Publication date Assignee Title
GB921032A (en) * 1958-11-27 1963-03-13 Tokyo Shibaura Electric Co A method of manufacturing antistatic record discs
FR1293186A (fr) * 1960-04-14 1962-05-11 Ici Ltd Polymères organiques à propriétés antistatiques améliorées
EP0134523A1 (de) * 1983-08-04 1985-03-20 General Electric Company Absorption von Additiven aus Lösungen in Polymeroberflächen
US4770905A (en) * 1986-12-23 1988-09-13 M&T Chemicals Inc. Process for surface modification of polymer articles

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994011421A1 (en) * 1992-11-06 1994-05-26 Pharmacia Biotech Ab A method of surface modification
US6156550A (en) * 1992-11-06 2000-12-05 Pharmacia Biotech Ab Method of non-adhesive coating of a synthetic polymer based surface with particles

Also Published As

Publication number Publication date
JPH05214130A (ja) 1993-08-24
US5169688A (en) 1992-12-08
CA2061605A1 (en) 1992-08-28

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